(1) Field of the Invention
This invention relates to novel phosphoric esters of carbapenem antibiotics presented by the formula ##STR2## wherein
R is a hydrogen atom, hydroxyl or hydroxysulfonyloxy, and their salts and a preparation method thereof.
(2) Description of the Prior Art
Antibiotic compounds having a generic structure of 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (carbapenem) ##STR3## are generally known to have high antimicrobial activity and strong beta-lactamase-inhibitory property. Various types of 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic derivatives have been prepared by fermentational, semi-synthetic or fully-synthetic methods. Some examples are thienamycin [J. Antibiotics 32, 1-12 (1979)], epithienamycins (Abstracts Nos. 80 and 81, 17th Interscience Conference on Antimicrobial Agents and Chemotherapy), N-acetylthienamycin (German Pat. No. 2652681, 1977), olivanates [J. Antibiotics 32, 287-304 (1979)], PS-5 [J. Antibiotics 32, 262-286 (1979)], PS-6 and PS-7, U.S. Pat. No. 4,368,203.
Some of the present inventors have disclosed in E.P.O. 48,999 that Streptomyces sp. OA-6129 produces hitherto-unknown carbapenem compounds designated antibiotics OA-6129A, OA-6129B and OA-6129C presented by the following formula: ##STR4## wherein
R is a hydrogen atom, hydroxyl or hydroxysulfonyloxy.
In addition to the fundamental nucleus of 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, the new carbapenem compounds have a pantetheinyl group at carbon 3 and an ethyl, 1-hydroxyethyl or 1-hydroxysulfonyloxyethyl group at carbon 6 respectively.